Hydrochloric Acid → HCID 20720201, compound

The resulting compound and 7-(1-ethylpiperazin-4-yl)-5-bromothieno[2,3-c]pyridine (0.21 g) were reacted in the same manner as in Example 300-4, to give a reaction solution containing 7-(4-ethylpiperazin-1-yl)-5-[4-(trans-4-acetoxytetrahydropyran-2-yl)phenyl]thieno[2,3-c]pyridine. To the resulting reaction solution were added ethyl acetate and 2N hydrochloric acid, and the resulting insoluble matters were filtered off. The aqueous layer was separated, while the organic layer was extracted with 2N hydrochloric acid. The aqueous layers were combined and washed with ethyl acetate twice. The pH of the solution was adjusted to pH 10 by adding a 8N aqueous solution of sodium hydroxide thereto, and then the solution was extracted with ethyl acetate twice. The extract was washed with brine, dried over magnesium sulfate and the solvent was evaporated. Methanol (10 ml) was added to the resulting residue and dissolved, followed by the addition of a 5N aqueous solution of sodium hydroxide solution (1 ml). The resulting solution was left as it was at room temperature for 1 hr, and then the solvent evaporated. Water was added thereto, and then the mixture was extracted with ethyl acetate thrice. The extract was washed with brine, dried over magnesium sulfate, and then the solvent was evaporated. The resulting residue was purified by NH silica gel column chromatography (ethyl acetate/n-hexane system), to give 0.18 g of the free compound of the title compound as a colorless amorphous.

1. customto give a reaction solution
2. customTo the resulting reaction solution
3. filtrationthe resulting insoluble matters were filtered off
4. customThe aqueous layer was separated, while the organic layer
5. extractionwas extracted with 2N hydrochloric acid
6. washwashed with ethyl acetate twice
7. additionby adding a 8N aqueous solution of sodium hydroxide
8. extractionthe solution was extracted with ethyl acetate twice
9. washThe extract was washed with brine
10. dry with materialdried over magnesium sulfate
11. customthe solvent was evaporated
12. additionMethanol (10 ml) was added to the resulting residue
13. dissolutiondissolved
14. additionfollowed by the addition of a 5N aqueous solution of sodium hydroxide solution (1 ml)
15. waitThe resulting solution was left as it
16. customthe solvent evaporated
17. additionWater was added
18. extractionthe mixture was extracted with ethyl acetate thrice
19. washThe extract was washed with brine
20. dry with materialdried over magnesium sulfate
21. customthe solvent was evaporated
22. customThe resulting residue was purified by NH silica gel column chromatography (ethyl acetate/n-hexane system)

ORD record

ord-cb5cc475c09442b6b33fb2e0f9f78cb9

Source dataset

uspto-grants-2004_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06790844B2